Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase
With the purpose of synthesizing free 2-thioglycosides of N-acetylneuraminic acid as potential inhibitors of trans-sialidases, a reinvestigation of glycosylation methods was performed. Treatment of methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-α,β-D-glycero-D- galacto-2-nonulopyranosid)oa...
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| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_03650375_v86_n3-6_p237_Marino |
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todo:paper_03650375_v86_n3-6_p237_Marino2023-10-03T15:27:53Z Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase Marino, C. Varela, O. De Lederkremer, R.M. With the purpose of synthesizing free 2-thioglycosides of N-acetylneuraminic acid as potential inhibitors of trans-sialidases, a reinvestigation of glycosylation methods was performed. Treatment of methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-α,β-D-glycero-D- galacto-2-nonulopyranosid)oate (1) with thiols in the presence of SnCl4, afforded the β-2-thioglycosides as major products. The methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-3,5-dideoxy-β-D-glycero-D- galacto-2-nonulopyranosid)oate (5) was prepared from 1 with trimethylsilyl bromide. This activated compound led to the 2-thio-α-glycosides when reacted with thiophenols, and to the β anomer by reaction with phenylmethanetiol. These products were characterized as the free ammonium salts. On the other hand, treatment of bromide 5, or the analogue chloride 2, with potassium thiocyanate in acetone led regioselectively to methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-isothiocyano-D-glycero-D- galacto-2-nonulopyranosid)oates, being the β-anomer 13 the major product. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03650375_v86_n3-6_p237_Marino |
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Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
With the purpose of synthesizing free 2-thioglycosides of N-acetylneuraminic acid as potential inhibitors of trans-sialidases, a reinvestigation of glycosylation methods was performed. Treatment of methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-α,β-D-glycero-D- galacto-2-nonulopyranosid)oate (1) with thiols in the presence of SnCl4, afforded the β-2-thioglycosides as major products. The methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-3,5-dideoxy-β-D-glycero-D- galacto-2-nonulopyranosid)oate (5) was prepared from 1 with trimethylsilyl bromide. This activated compound led to the 2-thio-α-glycosides when reacted with thiophenols, and to the β anomer by reaction with phenylmethanetiol. These products were characterized as the free ammonium salts. On the other hand, treatment of bromide 5, or the analogue chloride 2, with potassium thiocyanate in acetone led regioselectively to methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-isothiocyano-D-glycero-D- galacto-2-nonulopyranosid)oates, being the β-anomer 13 the major product. |
| format |
JOUR |
| author |
Marino, C. Varela, O. De Lederkremer, R.M. |
| spellingShingle |
Marino, C. Varela, O. De Lederkremer, R.M. Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| author_facet |
Marino, C. Varela, O. De Lederkremer, R.M. |
| author_sort |
Marino, C. |
| title |
Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| title_short |
Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| title_full |
Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| title_fullStr |
Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| title_full_unstemmed |
Synthesis of 2-thioglycosides and isothiocyanates of N-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| title_sort |
synthesis of 2-thioglycosides and isothiocyanates of n-acetylneuraminic acid as potential inhibitors of trans-sialidase |
| url |
http://hdl.handle.net/20.500.12110/paper_03650375_v86_n3-6_p237_Marino |
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| _version_ |
1782023739187134464 |